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One‐Pot Preparation of Aromatic Amides, 4‐Arylthiazoles, and 4‐Arylimidazoles from Arenes
Author(s) -
Yamamoto Takahiro,
Togo Hideo
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800730
Subject(s) - chemistry , aryl , organic chemistry , iodine , electrophilic aromatic substitution , medicinal chemistry , primary (astronomy) , aromaticity , molecule , alkyl , physics , astronomy
Simple treatment of arenes with α‐bromoacetyl chloride and AlCl 3 , followed by the reaction with molecular iodine and aq. NH 3 , thioamides, or amidines gave the corresponding primary aromatic amides, 4‐arylthiazoles, or 4‐arylimidazoles in good yields, respectively. Aryl α‐bromomethyl ketones are the key intermediates in those reactions. Primary aromatic amides were formed from arenes through the reaction of aryl α‐bromomethyl ketones with molecular iodine and aq. NH 3 , and 4‐arylthiazoles and 4‐arylimidazoles were formed from arenes through the reactions of aryl α‐bromomethyl ketones with thioamides and amidines, respectively, in one pot under transition‐metal‐free conditions.